4-[4-[(E)-C-methyl-N-phenylmethoxycarbonimidoyl]phenyl]-1,2,4-triazolidine-3,5-dione → 4-[4-[(E)-C-methyl-N-phenylmethoxycarbonimidoyl]phenyl]-1,2,4-triazole-3,5-dione

HRID 1746263Notes

Reaction equation

HRID 1746263 reaction equation
[CH2:1]([O:8]/[N:9]=[C:10](/[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:22](=[O:23])[NH:21][NH:20][C:19]2=[O:24])=[CH:14][CH:13]=1)\[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl>[CH2:1]([O:8]/[N:9]=[C:10](/[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:19](=[O:24])[N:20]=[N:21][C:22]2=[O:23])=[CH:14][CH:13]=1)\[CH3:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 893923334-[4-[(E)-C-methyl-N-phenylmethoxycarbonimidoyl]phenyl]-1,2,4-triazolidine-3,5-dione

Product 1

HCID 893923574-[4-[(E)-C-methyl-N-phenylmethoxycarbonimidoyl]phenyl]-1,2,4-triazole-3,5-dioneYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (E)-4-(4-(1-(benzyloxyimino)ethyl)phenyl)-1,2,4-triazolidine-3,5-dione (I-5a: 56 mg, 0.173 mmol) in CH2Cl2 (1.727 mL) was added SiO2—HNO3 (112 mg). The mixture was stirred at room temperature for 30 minutes, filtered, concentrated in vacuo and dried to give (E)-4-(4-(1-(benzyloxyimino)ethyl)phenyl)-3H-1,2,4-triazole-3,5(4H)-dione (I-4b: 29 mg, 52%) as a red solid. 1H NMR (400 MHz, CD3CN) δ ppm 2.31 (s, 3 H) 5.28 (s, 2 H) 7.38 (d, J=7.07 Hz, 1 H) 7.43 (t, J=7.20 Hz, 2 H) 7.46-7.54 (m, 4 H) 7.86-7.94 (m, 2 H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customdried

Sources & evidence

ORD record
ord-0ab91288c5e54a28adfd8b49f6c5e448
Source dataset
uspto-grants-2015_10
Patent number
US09149541B2

Reaction notes

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